Lithium hydroxide, monohydrate → 3-(Methyl(2-morpholinoethyl)carbamoyl)benzoic acid

HRID 926787Notes

Reaction equation

HRID 926787 reaction equation
[CH3:1][N:2]([CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10]C)=[O:9])=[O:4].O.[OH-].[Li+]>O1CCCC1.O>[CH3:1][N:2]([CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([OH:10])=[O:9])=[O:4]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66586820Methyl 3-(methyl(2-morpholinoethyl)carbamoyl)benzoate

Product 1

HCID 665869413-(Methyl(2-morpholinoethyl)carbamoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

Into a 100-mL round bottom flask, was placed a solution of methyl 3-(methyl(2-morpholinoethyl)carbamoyl)benzoate (4.4 g, 13.66 mmol, 1.00 equiv, 95%) in tetrahydrofuran/water (15/10 mL), and lithium hydroxide hydrate (1.77 g, 43.17 mmol, 3.00 equiv). The resulting solution was stirred for 1 h at 25° C. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 10 mL of water and adjusted to pH 2-3 with hydrochloric acid. The resulting mixture was washed with 2×30 mL of ethyl acetate. The aqueous layers were concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate:methanol (4:1). This resulted in 2.7 g (65%) of 3-(methyl(2-morpholinoethyl)carbamoyl)benzoic acid as a white solid. 1H-NMR (300 MHz, CD3OD, ppm): δ 8.17 (m, 2H), 7.78 (m, 1H), 7.61 (m, 1H), 3.98 (m, 6H), 3.56 (m, 5H), 3.47 (m, 1H), 3.10 (s, 3H). MS (ES, m/z): 293 [M+H]+.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe resulting solution was diluted with 10 mL of water
  4. washThe resulting mixture was washed with 2×30 mL of ethyl acetate
  5. concentrationThe aqueous layers were concentrated under vacuum
  6. washeluted with ethyl acetate:methanol (4:1)
  7. customThis resulted in 2.7 g (65%) of 3-(methyl(2-morpholinoethyl)carbamoyl)benzoic acid as a white solid

Sources & evidence

ORD record
ord-ec4a0159114b4d039cdec405cb5b9393
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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